Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Maria Gdaniec'
_publ_contact_author_address     
;
Faculty of Chemistry
Adam Mickiewicz University
Poznan
60-780
POLAND

;

_publ_contact_author_email       MAGDAN@AMU.EDU.PL

_publ_section_title              
;
Co-crystals of iodopentafluorobenzene with nitrogen
donors: 2D molecular assemblies through halogen bonding and
aryl-perfluoroaryl interactions
;
loop_
_publ_author_name
M.Gdaniec
T.Polonski
A.Wasilewska

data_1.2
_database_code_depnum_ccdc_archive 'CCDC 618383'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,4,6-trimethylpyridine pentafluoroiodobenzene
;
_chemical_name_common            
'2,4,6-trimethylpyridine pentafluoroiodobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C8 H11 N'
_chemical_formula_sum            'C14 H11 F5 I N'
_chemical_formula_weight         415.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.5677(4)
_cell_length_b                   16.7343(6)
_cell_length_c                   11.6003(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1469.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3251
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5803
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         26.35
_reflns_number_total             1501
_reflns_number_gt                1191
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3
(Bruno et al., 2002)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.4024P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1501
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.652542(11) 0.2500 0.01996(10) Uani 1 2 d S . .
F2 F 0.64670(16) 0.52142(8) 0.43019(10) 0.0284(3) Uani 1 1 d . . .
F3 F 0.6432(2) 0.36063(8) 0.43057(12) 0.0401(4) Uani 1 1 d . . .
F4 F 0.5000 0.27904(13) 0.2500 0.0468(6) Uani 1 2 d S . .
C1 C 0.5000 0.52640(18) 0.2500 0.0186(6) Uani 1 2 d S . .
C2 C 0.5724(3) 0.48315(13) 0.34012(17) 0.0214(5) Uani 1 1 d . . .
C3 C 0.5722(3) 0.40065(14) 0.3416(2) 0.0273(5) Uani 1 1 d . . .
C4 C 0.5000 0.35939(19) 0.2500 0.0276(8) Uani 1 2 d S . .
N1A N 0.5000 0.82363(17) 0.2500 0.0200(5) Uani 1 2 d S . .
C2A C 0.5608(3) 0.86485(14) 0.1583(2) 0.0245(5) Uani 1 1 d . . .
C3A C 0.5615(3) 0.94767(14) 0.15583(19) 0.0246(5) Uani 1 1 d . . .
H3A H 0.6033 0.9744 0.0910 0.030 Uiso 1 1 calc R . .
C4A C 0.5000 0.9910(2) 0.2500 0.0246(7) Uani 1 2 d S . .
C5A C 0.6249(3) 0.81649(14) 0.05737(19) 0.0338(6) Uani 1 1 d . . .
H5A H 0.7110 0.7728 0.0976 0.041 Uiso 1 1 d R . .
H5BA H 0.5269 0.7877 0.0211 0.041 Uiso 1 1 d R . .
H5CA H 0.7020 0.8466 0.0052 0.041 Uiso 1 1 d R . .
C6A C 0.5000 1.0806(2) 0.2500 0.0332(8) Uani 1 2 d S . .
H6AC H 0.5477 1.0963 0.3231 0.040 Uiso 0.50 1 d PR . .
H6AD H 0.5853 1.0963 0.1932 0.040 Uiso 0.50 1 d PR . .
H6AE H 0.4107 1.1103 0.2390 0.040 Uiso 0.50 1 d PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01870(13) 0.01716(14) 0.02402(13) 0.000 0.00095(8) 0.000
F2 0.0280(7) 0.0346(7) 0.0227(6) 0.0013(6) -0.0036(5) -0.0030(6)
F3 0.0446(9) 0.0354(8) 0.0403(8) 0.0197(7) 0.0036(7) 0.0072(7)
F4 0.0629(16) 0.0126(10) 0.0648(15) 0.000 0.0151(11) 0.000
C1 0.0148(13) 0.0194(16) 0.0215(14) 0.000 0.0069(12) 0.000
C2 0.0183(10) 0.0246(12) 0.0211(11) -0.0002(9) 0.0029(9) -0.0018(10)
C3 0.0243(11) 0.0271(12) 0.0303(12) 0.0092(10) 0.0079(11) 0.0052(11)
C4 0.0308(19) 0.0129(16) 0.039(2) 0.000 0.0116(15) 0.000
N1A 0.0216(13) 0.0174(12) 0.0209(13) 0.000 0.0005(11) 0.000
C2A 0.0220(11) 0.0260(12) 0.0254(11) 0.0027(10) -0.0018(10) -0.0035(10)
C3A 0.0210(10) 0.0238(12) 0.0290(11) 0.0058(10) -0.0027(9) -0.0041(10)
C4A 0.0153(14) 0.0191(16) 0.0393(18) 0.000 -0.0087(14) 0.000
C5A 0.0463(16) 0.0300(14) 0.0251(12) -0.0012(10) 0.0105(11) -0.0071(11)
C6A 0.0204(16) 0.0262(19) 0.053(2) 0.000 -0.0061(16) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.111(3) . ?
F2 C2 1.348(2) . ?
F3 C3 1.343(3) . ?
F4 C4 1.344(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.380(3) . ?
N1A C2A 1.349(3) . ?
C2A C3A 1.386(3) . ?
C2A C5A 1.504(3) . ?
C3A C4A 1.391(3) . ?
C3A H3A 0.9300 . ?
C4A C6A 1.500(5) . ?
C5A H5A 1.0852 . ?
C5A H5BA 0.9796 . ?
C5A H5CA 0.9794 . ?
C6A H6AC 0.9585 . ?
C6A H6AD 0.9585 . ?
C6A H6AE 0.8478 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 117.0(3) 3_655 . ?
C2 C1 I1 121.52(14) . . ?
F2 C2 C3 117.8(2) . . ?
F2 C2 C1 120.13(19) . . ?
C3 C2 C1 122.1(2) . . ?
F3 C3 C4 120.1(2) . . ?
F3 C3 C2 120.5(2) . . ?
C4 C3 C2 119.5(2) . . ?
F4 C4 C3 120.04(15) . . ?
C3 C4 C3 119.9(3) 3_655 . ?
C2A N1A C2A 118.5(3) . 3_655 ?
N1A C2A C3A 121.9(2) . . ?
N1A C2A C5A 116.7(2) . . ?
C3A C2A C5A 121.4(2) . . ?
C2A C3A C4A 120.2(2) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C3A C4A C3A 117.2(3) . 3_655 ?
C3A C4A C6A 121.40(16) . . ?
C2A C5A H5A 102.8 . . ?
C2A C5A H5BA 110.8 . . ?
H5A C5A H5BA 107.9 . . ?
C2A C5A H5CA 113.4 . . ?
H5A C5A H5CA 104.8 . . ?
H5BA C5A H5CA 116.0 . . ?
C4A C6A H6AC 105.8 . . ?
C4A C6A H6AD 105.8 . . ?
H6AC C6A H6AD 106.2 . . ?
C4A C6A H6AE 125.8 . . ?
H6AC C6A H6AE 105.9 . . ?
H6AD C6A H6AE 105.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.084

#===END

data_1-3
_database_code_depnum_ccdc_archive 'CCDC 618384'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,6-dimethylpyridine pentafluoroiodobenzene 1/1 adduct
;
_chemical_name_common            
'2,6-dimethylpyridine pentafluoroiodobenzene 1/1 adduct'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C7 H9 N'
_chemical_formula_sum            'C13 H9 F5 I N'
_chemical_formula_weight         401.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'

_cell_length_a                   7.3936(9)
_cell_length_b                   15.4467(19)
_cell_length_c                   12.0105(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.881(10)
_cell_angle_gamma                90.00
_cell_volume                     1371.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2546
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .414
_exptl_absorpt_correction_T_max  .490
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
crystals unstable in air
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4193
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1396
_reflns_number_gt                1306
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3
(Bruno et al., 2002)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+0.0223P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1396
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0454
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.652372(11) 0.7500 0.02896(10) Uani 1 2 d S . .
F2 F 0.35771(18) 0.51158(9) 0.57264(11) 0.0345(3) Uani 1 1 d . . .
F3 F 0.3604(2) 0.33793(9) 0.57243(15) 0.0498(4) Uani 1 1 d . . .
F4 F 0.5000 0.24962(12) 0.7500 0.0635(7) Uani 1 2 d S . .
C1 C 0.5000 0.51677(18) 0.7500 0.0218(6) Uani 1 2 d S . .
C2 C 0.4295(3) 0.47011(14) 0.66091(17) 0.0246(5) Uani 1 1 d . . .
C3 C 0.4290(3) 0.38151(16) 0.6602(2) 0.0327(5) Uani 1 1 d . . .
C4 C 0.5000 0.33698(18) 0.7500 0.0361(8) Uani 1 2 d S . .
N1A N 0.5000 0.84406(13) 0.7500 0.0220(5) Uani 1 2 d S . .
C2A C 0.4461(3) 0.88888(13) 0.65886(16) 0.0225(4) Uani 1 1 d . . .
C3A C 0.4429(3) 0.97839(13) 0.65708(17) 0.0237(4) Uani 1 1 d . . .
H3AA H 0.4023 1.0072 0.5934 0.028 Uiso 1 1 calc R . .
C4A C 0.5000 1.02585(19) 0.7500 0.0193(6) Uani 1 2 d S . .
H4AA H 0.5000 1.0861 0.7500 0.023 Uiso 1 2 calc SR . .
C5A C 0.3916(3) 0.83596(14) 0.5588(2) 0.0316(5) Uani 1 1 d G . .
H5AA H 0.3018 0.7946 0.5798 0.047 Uiso 1 1 calc G . .
H5AB H 0.4966 0.8062 0.5329 0.047 Uiso 1 1 calc G . .
H5AC H 0.3439 0.8722 0.5005 0.047 Uiso 1 1 calc G . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02715(14) 0.02199(13) 0.03778(15) 0.000 0.00199(8) 0.000
F2 0.0287(7) 0.0494(8) 0.0253(7) -0.0002(6) -0.0028(5) 0.0055(6)
F3 0.0395(9) 0.0499(9) 0.0601(10) -0.0327(7) 0.0002(8) -0.0040(6)
F4 0.0580(15) 0.0186(10) 0.114(2) 0.000 0.0063(14) 0.000
C1 0.0165(14) 0.0217(14) 0.0274(15) 0.000 0.0044(12) 0.000
C2 0.0176(11) 0.0318(12) 0.0245(11) -0.0013(8) 0.0021(8) 0.0026(8)
C3 0.0215(11) 0.0323(12) 0.0445(14) -0.0149(10) 0.0055(10) -0.0020(9)
C4 0.0256(17) 0.0202(16) 0.063(2) 0.000 0.0101(16) 0.000
N1A 0.0213(13) 0.0194(12) 0.0251(13) 0.000 -0.0025(10) 0.000
C2A 0.0178(10) 0.0244(11) 0.0253(11) -0.0008(8) -0.0004(8) -0.0002(8)
C3A 0.0201(11) 0.0262(11) 0.0249(11) 0.0055(8) 0.0026(9) 0.0035(8)
C4A 0.0131(13) 0.0236(14) 0.0213(14) 0.000 0.0053(11) 0.000
C5A 0.0353(13) 0.0311(12) 0.0282(12) -0.0032(9) -0.0089(10) 0.0038(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.095(3) . ?
F2 C2 1.341(2) . ?
F3 C3 1.344(3) . ?
F4 C4 1.350(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.376(3) . ?
N1A C2A 1.350(2) . ?
C2A C3A 1.383(3) . ?
C2A C5A 1.503(3) . ?
C3A C4A 1.395(3) . ?
C3A H3AA 0.9300 . ?
C4A H4AA 0.9300 . ?
C5A H5AA 0.9582 . ?
C5A H5AB 0.9582 . ?
C5A H5AC 0.9587 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 117.3(3) . 6_657 ?
C2 C1 I1 121.35(13) . . ?
F2 C2 C3 118.17(19) . . ?
F2 C2 C1 120.12(19) . . ?
C3 C2 C1 121.7(2) . . ?
F3 C3 C2 120.4(2) . . ?
F3 C3 C4 120.0(2) . . ?
C2 C3 C4 119.6(2) . . ?
F4 C4 C3 119.99(14) . . ?
C3 C4 C3 120.0(3) 6_657 . ?
C2A N1A C2A 118.3(2) 6_657 . ?
N1A C2A C3A 122.00(19) . . ?
N1A C2A C5A 116.20(19) . . ?
C3A C2A C5A 121.80(19) . . ?
C2A C3A C4A 120.5(2) . . ?
C2A C3A H3AA 119.7 . . ?
C4A C3A H3AA 119.7 . . ?
C3A C4A C3A 116.6(3) . 6_657 ?
C3A C4A H4AA 121.7 . . ?
C2A C5A H5AA 109.3 . . ?
C2A C5A H5AB 108.2 . . ?
H5AA C5A H5AB 109.5 . . ?
C2A C5A H5AC 110.9 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.066

#===END

data_1.4
_database_code_depnum_ccdc_archive 'CCDC 618385'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3,5-dimethlpyridine pentafluoroiodobenzene
;
_chemical_name_common            '3,5-dimethlpyridine pentafluoroiodobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C7 H9 N'
_chemical_formula_sum            'C13 H9 F5 I N'
_chemical_formula_weight         401.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'

_cell_length_a                   7.2401(8)
_cell_length_b                   15.1648(14)
_cell_length_c                   12.9908(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.574(8)
_cell_angle_gamma                90.00
_cell_volume                     1425.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2958
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .46
_exptl_absorpt_correction_T_max  .52
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4435
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1448
_reflns_number_gt                1353
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3
(Bruno et al., 2002)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+2.2675P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1448
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.293643(17) 0.2500 0.04534(12) Uani 1 2 d S . .
F2 F 0.6228(3) 0.15068(18) 0.41961(17) 0.0710(6) Uani 1 1 d . . .
F3 F 0.6270(4) -0.0259(2) 0.4189(3) 0.1247(15) Uani 1 1 d . . .
F4 F 0.5000 -0.1158(2) 0.2500 0.159(3) Uani 1 2 d S . .
C1 C 0.5000 0.1531(3) 0.2500 0.0421(9) Uani 1 2 d S . .
C2 C 0.5614(4) 0.1081(2) 0.3350(3) 0.0506(8) Uani 1 1 d . . .
C3 C 0.5623(5) 0.0178(3) 0.3347(4) 0.0764(15) Uani 1 1 d . . .
C4 C 0.5000 -0.0272(4) 0.2500 0.095(3) Uani 1 2 d S . .
N1A N 0.5000 0.4803(2) 0.2500 0.0490(9) Uani 1 2 d S . .
C2A C 0.4527(4) 0.5247(2) 0.1655(2) 0.0425(7) Uani 1 1 d . . .
H2AA H 0.4173 0.4919 0.1049 0.051 Uiso 1 1 d R . .
C3A C 0.4517(4) 0.6156(2) 0.1606(2) 0.0377(6) Uani 1 1 d . . .
C4A C 0.5000 0.6611(3) 0.2500 0.0359(8) Uani 1 2 d S . .
H4AA H 0.5000 0.7245 0.2500 0.043 Uiso 1 2 d SR . .
C5A C 0.4003(5) 0.6644(3) 0.0638(3) 0.0586(9) Uani 1 1 d . . .
H5AA H 0.4095 0.7266 0.0771 0.070 Uiso 1 1 d R . .
H5AB H 0.2730 0.6519 0.0470 0.070 Uiso 1 1 d R . .
H5AC H 0.4565 0.6542 0.0168 0.070 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04912(19) 0.03843(17) 0.04883(19) 0.000 0.00814(12) 0.000
F2 0.0568(13) 0.0981(18) 0.0580(13) 0.0201(12) -0.0020(10) 0.0063(12)
F3 0.089(2) 0.105(2) 0.183(4) 0.096(2) 0.047(2) 0.0395(17)
F4 0.113(4) 0.0303(16) 0.337(9) 0.000 0.097(5) 0.000
C1 0.0207(17) 0.060(3) 0.046(2) 0.000 0.0093(15) 0.000
C2 0.0300(14) 0.0583(19) 0.064(2) 0.0169(16) 0.0073(14) 0.0054(13)
C3 0.044(2) 0.055(2) 0.132(4) 0.042(3) 0.033(2) 0.0148(17)
C4 0.057(3) 0.033(3) 0.198(9) 0.000 0.058(5) 0.000
N1A 0.050(2) 0.0370(19) 0.061(2) 0.000 0.0070(18) 0.000
C2A 0.0376(15) 0.0458(16) 0.0443(17) -0.0121(13) 0.0046(12) -0.0002(12)
C3A 0.0317(13) 0.0444(15) 0.0369(15) -0.0002(12) 0.0018(11) 0.0016(11)
C4A 0.0320(19) 0.0307(19) 0.045(2) 0.000 0.0004(16) 0.000
C5A 0.061(2) 0.073(2) 0.0418(18) 0.0064(17) -0.0062(15) 0.0071(18)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.131(5) . ?
F2 C2 1.340(5) . ?
F3 C3 1.352(6) . ?
F4 C4 1.344(7) . ?
C1 C2 1.363(4) . ?
C2 C3 1.368(5) . ?
C3 C4 1.361(6) . ?
N1A C2A 1.325(4) . ?
C2A C3A 1.380(4) . ?
C3A C4A 1.387(3) . ?
C3A C5A 1.498(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 119.8(5) . 6_656 ?
C2 C1 I1 120.1(2) . . ?
F2 C2 C1 121.1(3) . . ?
F2 C2 C3 118.9(4) . . ?
C1 C2 C3 120.0(4) . . ?
F3 C3 C4 120.5(4) . . ?
F3 C3 C2 119.3(5) . . ?
C4 C3 C2 120.2(5) . . ?
F4 C4 C3 120.1(3) . . ?
C3 C4 C3 119.8(5) . 6_656 ?
C2A N1A C2A 118.9(4) 6_656 . ?
N1A C2A C3A 123.1(3) . . ?
C2A C3A C4A 117.2(3) . . ?
C2A C3A C5A 122.2(3) . . ?
C4A C3A C5A 120.6(3) . . ?
C3A C4A C3A 120.3(4) . 6_656 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.081

#===END

data_1.4lt
_database_code_depnum_ccdc_archive 'CCDC 618386'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3,5-dimethylpyridine pentafluoroiodobenzene
;
_chemical_name_common            '3,5-dimethylpyridine pentafluoroiodobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F 5I, C7 H9 N'
_chemical_formula_sum            'C13 H9 F5 I N'
_chemical_formula_weight         401.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x+1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2792(5)
_cell_length_b                   12.9453(7)
_cell_length_c                   15.2214(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.479(6)
_cell_angle_gamma                90.00
_cell_volume                     1427.78(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2877
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
low-temperature phase (phase transition at 168K) is twinned
with the twin matrix -1 0 0 0 -1 0 0.4024 0 1.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2149
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2149
_reflns_number_gt                2039
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3
(Bruno et al., 2002)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
The crystal is a twin as a result of the phase transition at 168K. It has been
refined with hklf 5 instruction with shelxl-98. Low data completness
results
from removal of reflections for which a correct peak integration
could not be done. The BASF parameter value refined at 0.462.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0905P)^2^+15.3689P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2149
_refine_ls_number_parameters     182
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1881
_refine_ls_wR_factor_gt          0.1865
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.5160(19) 0.2577(8) 0.4801(6) 0.034(3) Uani 1 1 d . . .
C2A C 0.4711(18) 0.1724(9) 0.5218(8) 0.025(3) Uani 1 1 d . . .
H2A H 0.4403 0.1139 0.4880 0.030 Uiso 1 1 d R . .
C3A C 0.4687(18) 0.1658(8) 0.6128(7) 0.020(2) Uani 1 1 d U . .
C4A C 0.5183(15) 0.2567(9) 0.6610(7) 0.021(2) Uani 1 1 d . . .
H4A H 0.5204 0.2560 0.7222 0.025 Uiso 1 1 d R . .
C5A C 0.5644(17) 0.3457(8) 0.6197(7) 0.020(2) Uani 1 1 d U . .
C6A C 0.562(2) 0.3423(10) 0.5268(8) 0.028(3) Uani 1 1 d . . .
H6A H 0.5954 0.4014 0.4974 0.034 Uiso 1 1 d R . .
C7A C 0.418(2) 0.0680(11) 0.6584(11) 0.037(3) Uani 1 1 d . . .
H7AC H 0.3880 0.0149 0.6154 0.056 Uiso 1 1 d R . .
H7AB H 0.3125 0.0815 0.6901 0.056 Uiso 1 1 d R . .
H7AA H 0.5192 0.0457 0.6989 0.056 Uiso 1 1 d R . .
C8A C 0.613(3) 0.4435(11) 0.6706(9) 0.040(4) Uani 1 1 d . . .
H8AC H 0.6064 0.4319 0.7325 0.060 Uiso 1 1 d R . .
H8AB H 0.5274 0.4972 0.6507 0.060 Uiso 1 1 d R . .
H8AA H 0.7355 0.4639 0.6603 0.060 Uiso 1 1 d R . .
I1 I 0.51872(11) 0.25118(6) 0.29366(4) 0.0247(3) Uani 1 1 d . . .
F2 F 0.4003(13) 0.4134(5) 0.1369(5) 0.0334(18) Uani 1 1 d . . .
F3 F 0.4029(15) 0.4031(7) -0.0403(5) 0.050(2) Uani 1 1 d . . .
F4 F 0.5316(15) 0.2285(9) -0.1164(5) 0.059(3) Uani 1 1 d . . .
F5 F 0.6524(14) 0.0634(6) -0.0140(5) 0.044(2) Uani 1 1 d . . .
F6 F 0.6398(15) 0.0715(6) 0.1629(5) 0.041(2) Uani 1 1 d . . .
C1 C 0.5209(14) 0.2425(8) 0.1534(7) 0.020(2) Uani 1 1 d . . .
C2 C 0.4610(19) 0.3266(9) 0.1006(7) 0.023(2) Uani 1 1 d . . .
C3 C 0.466(2) 0.3220(11) 0.0105(8) 0.032(3) Uani 1 1 d . . .
C4 C 0.526(3) 0.2325(13) -0.0274(8) 0.049(4) Uani 1 1 d . . .
C5 C 0.585(2) 0.1501(11) 0.0244(9) 0.033(3) Uani 1 1 d . . .
C6 C 0.5808(19) 0.1553(9) 0.1133(8) 0.026(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.053(7) 0.034(5) 0.016(4) 0.000(4) 0.003(5) 0.008(7)
C2A 0.014(5) 0.031(6) 0.031(6) -0.005(5) 0.001(5) 0.002(5)
C3A 0.020(2) 0.021(2) 0.020(2) 0.0003(10) 0.0020(10) -0.0003(10)
C4A 0.017(5) 0.027(5) 0.020(5) 0.008(5) 0.003(4) 0.007(6)
C5A 0.020(2) 0.020(2) 0.020(2) 0.0001(10) 0.0019(10) 0.0003(10)
C6A 0.031(7) 0.031(6) 0.024(6) 0.006(5) 0.001(6) 0.010(6)
C7A 0.025(7) 0.037(7) 0.050(9) 0.010(6) 0.003(7) -0.005(6)
C8A 0.046(10) 0.036(7) 0.036(7) -0.009(6) -0.001(8) -0.001(8)
I1 0.0281(4) 0.0299(4) 0.0161(4) -0.0009(3) 0.0028(3) -0.0016(4)
F2 0.032(4) 0.025(3) 0.043(4) 0.004(3) -0.001(4) 0.001(4)
F3 0.046(6) 0.061(5) 0.041(5) 0.028(4) -0.004(4) -0.013(5)
F4 0.053(6) 0.113(8) 0.013(3) 0.000(4) 0.009(4) -0.003(6)
F5 0.036(5) 0.053(5) 0.045(5) -0.026(4) 0.015(4) 0.000(4)
F6 0.054(6) 0.027(4) 0.041(4) -0.001(3) 0.003(5) 0.009(4)
C1 0.014(4) 0.017(5) 0.030(5) 0.005(5) 0.011(4) -0.005(5)
C2 0.021(6) 0.024(5) 0.025(6) 0.005(4) 0.006(5) 0.005(5)
C3 0.019(6) 0.056(8) 0.021(6) 0.018(6) 0.003(5) 0.002(6)
C4 0.057(10) 0.076(11) 0.011(5) -0.008(6) -0.008(7) -0.023(10)
C5 0.024(7) 0.044(7) 0.033(7) -0.014(6) 0.007(6) -0.008(6)
C6 0.024(6) 0.024(6) 0.029(6) 0.001(5) 0.002(6) -0.004(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.330(16) . ?
N1A C6A 1.331(16) . ?
C2A C3A 1.390(16) . ?
C3A C4A 1.416(15) . ?
C3A C7A 1.507(17) . ?
C4A C5A 1.370(15) . ?
C5A C6A 1.412(16) . ?
C5A C8A 1.508(17) . ?
I1 C1 2.140(11) . ?
F2 C2 1.346(14) . ?
F3 C3 1.358(15) . ?
F4 C4 1.360(14) . ?
F5 C5 1.376(16) . ?
F6 C6 1.368(14) . ?
C1 C6 1.374(17) . ?
C1 C2 1.398(15) . ?
C2 C3 1.376(16) . ?
C3 C4 1.38(2) . ?
C4 C5 1.37(2) . ?
C5 C6 1.358(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A N1A C6A 119.3(10) . . ?
N1A C2A C3A 123.6(11) . . ?
C2A C3A C4A 116.0(10) . . ?
C2A C3A C7A 122.5(11) . . ?
C4A C3A C7A 121.4(11) . . ?
C5A C4A C3A 121.5(10) . . ?
C4A C5A C6A 116.9(10) . . ?
C4A C5A C8A 121.7(11) . . ?
C6A C5A C8A 121.4(11) . . ?
N1A C6A C5A 122.6(11) . . ?
C6 C1 C2 118.6(11) . . ?
C6 C1 I1 121.3(8) . . ?
C2 C1 I1 120.1(8) . . ?
F2 C2 C3 119.1(11) . . ?
F2 C2 C1 120.7(10) . . ?
C3 C2 C1 120.2(11) . . ?
F3 C3 C2 119.6(13) . . ?
F3 C3 C4 120.9(12) . . ?
C2 C3 C4 119.4(12) . . ?
F4 C4 C5 120.3(15) . . ?
F4 C4 C3 119.2(14) . . ?
C5 C4 C3 120.4(11) . . ?
C6 C5 C4 119.9(13) . . ?
C6 C5 F5 120.5(13) . . ?
C4 C5 F5 119.7(12) . . ?
C5 C6 F6 118.3(12) . . ?
C5 C6 C1 121.5(12) . . ?
F6 C6 C1 120.2(11) . . ?

_diffrn_measured_fraction_theta_max 0.852
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.852
_refine_diff_density_max         2.736
_refine_diff_density_min         -1.550
_refine_diff_density_rms         0.198

# Formatted by publCIF

#===END

data_1.5
_database_code_depnum_ccdc_archive 'CCDC 618387'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-methylpyridine pentafluoroiodobenzene
;
_chemical_name_common            '4-methylpyridine pentafluoroiodobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C6 H7 N'
_chemical_formula_sum            'C12 H7 F5 I N'
_chemical_formula_weight         387.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2888(6)
_cell_length_b                   14.1251(11)
_cell_length_c                   12.6561(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.502(7)
_cell_angle_gamma                90.00
_cell_volume                     1297.01(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2677
_cell_measurement_theta_min      4
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .325
_exptl_absorpt_correction_T_max  .605
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7937
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2633
_reflns_number_gt                2247
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_cell_refinement       
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_data_reduction        
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
; Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3
(Bruno et al., 2002)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.6843P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2633
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21918(2) 0.554691(12) 0.713602(15) 0.02587(9) Uani 1 1 d . . .
F2 F 0.0694(2) 0.66127(12) 0.49622(14) 0.0335(4) Uani 1 1 d . . .
F3 F 0.0410(2) 0.84484(13) 0.44341(14) 0.0392(5) Uani 1 1 d . . .
F4 F 0.1683(3) 0.98079(13) 0.58535(18) 0.0463(5) Uani 1 1 d . . .
F5 F 0.3135(3) 0.93063(13) 0.78264(17) 0.0427(5) Uani 1 1 d . . .
F6 F 0.3383(2) 0.74698(13) 0.83825(14) 0.0330(4) Uani 1 1 d . . .
C1 C 0.2051(4) 0.69798(19) 0.6689(2) 0.0220(6) Uani 1 1 d . . .
C2 C 0.1314(4) 0.7265(2) 0.5692(2) 0.0240(6) Uani 1 1 d . . .
C3 C 0.1175(4) 0.8205(2) 0.5401(2) 0.0279(6) Uani 1 1 d . . .
C4 C 0.1802(4) 0.8891(2) 0.6121(3) 0.0300(7) Uani 1 1 d . . .
C5 C 0.2538(4) 0.8638(2) 0.7127(3) 0.0296(7) Uani 1 1 d . . .
C6 C 0.2670(4) 0.7690(2) 0.7399(2) 0.0252(6) Uani 1 1 d . . .
N1A N 0.2583(3) 0.36978(18) 0.79370(19) 0.0269(6) Uani 1 1 d . . .
C2A C 0.2312(4) 0.2844(2) 0.7482(3) 0.0291(7) Uani 1 1 d . . .
H2AA H 0.1848 0.2821 0.6772 0.035 Uiso 1 1 calc R . .
C3A C 0.2684(4) 0.1998(2) 0.8006(2) 0.0272(7) Uani 1 1 d . . .
H3AA H 0.2488 0.1426 0.7649 0.033 Uiso 1 1 calc R . .
C4A C 0.3356(4) 0.2008(2) 0.9074(2) 0.0258(6) Uani 1 1 d . . .
C5A C 0.3636(4) 0.2893(2) 0.9545(3) 0.0287(7) Uani 1 1 d . . .
H5AA H 0.4086 0.2939 1.0256 0.034 Uiso 1 1 calc R . .
C6A C 0.3246(4) 0.3699(2) 0.8954(3) 0.0286(6) Uani 1 1 d . . .
H6AA H 0.3459 0.4282 0.9286 0.034 Uiso 1 1 calc R . .
C7A C 0.3755(5) 0.1109(2) 0.9689(3) 0.0380(8) Uani 1 1 d G . .
H7AA H 0.3924 0.1251 1.0434 0.057 Uiso 1 1 calc G . .
H7AB H 0.2703 0.0703 0.9548 0.057 Uiso 1 1 calc G . .
H7AC H 0.4834 0.0796 0.9480 0.057 Uiso 1 1 calc G . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02834(13) 0.02333(12) 0.02661(13) 0.00403(8) 0.00612(8) 0.00301(7)
F2 0.0387(10) 0.0368(10) 0.0240(9) -0.0034(8) -0.0017(8) -0.0014(8)
F3 0.0425(11) 0.0465(11) 0.0282(10) 0.0144(8) 0.0007(8) 0.0120(9)
F4 0.0561(13) 0.0240(9) 0.0593(14) 0.0122(9) 0.0080(10) 0.0065(9)
F5 0.0479(12) 0.0314(10) 0.0478(13) -0.0119(9) -0.0010(10) -0.0073(8)
F6 0.0341(9) 0.0371(10) 0.0263(10) -0.0003(8) -0.0050(8) -0.0019(8)
C1 0.0204(13) 0.0230(14) 0.0230(15) 0.0009(12) 0.0038(11) 0.0004(11)
C2 0.0197(13) 0.0276(14) 0.0248(15) 0.0018(12) 0.0026(11) -0.0016(11)
C3 0.0221(14) 0.0349(16) 0.0272(16) 0.0086(13) 0.0048(12) 0.0048(12)
C4 0.0259(15) 0.0233(15) 0.0417(19) 0.0047(13) 0.0077(13) 0.0011(12)
C5 0.0240(15) 0.0283(16) 0.0369(18) -0.0057(13) 0.0043(13) -0.0014(12)
C6 0.0172(13) 0.0357(16) 0.0218(15) 0.0039(13) -0.0038(11) 0.0022(12)
N1A 0.0281(13) 0.0266(13) 0.0262(14) 0.0038(11) 0.0040(11) 0.0009(10)
C2A 0.0213(14) 0.0405(18) 0.0254(16) 0.0012(14) 0.0021(12) -0.0005(12)
C3A 0.0265(15) 0.0259(15) 0.0300(18) -0.0010(12) 0.0060(13) -0.0036(11)
C4A 0.0216(14) 0.0261(14) 0.0310(17) 0.0049(12) 0.0094(12) 0.0044(11)
C5A 0.0267(15) 0.0340(16) 0.0254(16) 0.0016(13) 0.0025(12) 0.0035(12)
C6A 0.0274(15) 0.0248(14) 0.0336(17) -0.0027(13) 0.0031(13) -0.0003(12)
C7A 0.0440(19) 0.0296(17) 0.042(2) 0.0097(15) 0.0143(15) 0.0103(14)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.101(3) . ?
F2 C2 1.351(3) . ?
F3 C3 1.340(3) . ?
F4 C4 1.339(3) . ?
F5 C5 1.338(3) . ?
F6 C6 1.339(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.383(4) . ?
N1A C6A 1.331(4) . ?
N1A C2A 1.343(4) . ?
C2A C3A 1.381(4) . ?
C2A H2AA 0.9300 . ?
C3A C4A 1.393(4) . ?
C3A H3AA 0.9300 . ?
C4A C5A 1.391(4) . ?
C4A C7A 1.503(4) . ?
C5A C6A 1.378(4) . ?
C5A H5AA 0.9300 . ?
C6A H6AA 0.9300 . ?
C7A H7AA 0.9599 . ?
C7A H7AB 0.9610 . ?
C7A H7AC 0.9615 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.9(3) . . ?
C2 C1 I1 122.1(2) . . ?
C6 C1 I1 121.1(2) . . ?
F2 C2 C3 117.6(3) . . ?
F2 C2 C1 120.0(2) . . ?
C3 C2 C1 122.4(3) . . ?
F3 C3 C4 120.4(3) . . ?
F3 C3 C2 120.3(3) . . ?
C4 C3 C2 119.3(3) . . ?
F4 C4 C3 120.3(3) . . ?
F4 C4 C5 119.5(3) . . ?
C3 C4 C5 120.2(3) . . ?
F5 C5 C4 120.0(3) . . ?
F5 C5 C6 120.5(3) . . ?
C4 C5 C6 119.4(3) . . ?
F6 C6 C5 117.9(3) . . ?
F6 C6 C1 120.3(3) . . ?
C5 C6 C1 121.8(3) . . ?
C6A N1A C2A 116.2(3) . . ?
N1A C2A C3A 123.9(3) . . ?
N1A C2A H2AA 118.1 . . ?
C3A C2A H2AA 118.1 . . ?
C2A C3A C4A 119.4(3) . . ?
C2A C3A H3AA 120.3 . . ?
C4A C3A H3AA 120.3 . . ?
C5A C4A C3A 116.7(3) . . ?
C5A C4A C7A 121.6(3) . . ?
C3A C4A C7A 121.7(3) . . ?
C6A C5A C4A 119.7(3) . . ?
C6A C5A H5AA 120.1 . . ?
C4A C5A H5AA 120.1 . . ?
N1A C6A C5A 124.1(3) . . ?
N1A C6A H6AA 117.9 . . ?
C5A C6A H6AA 117.9 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 107.3 . . ?
H7AA C7A H7AB 109.4 . . ?
C4A C7A H7AC 111.7 . . ?
H7AA C7A H7AC 109.6 . . ?
H7AB C7A H7AC 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.091

#===END


